Starfish saponins. Part XLII. Isolation of twelve steroidal glycosides from the Pacific Ocean starfish Henricia laeviuscola

The complete steroid glycosides anal. of the starfish H. laeviuscola, collected off the Gulf of California, is reported. Different steroid glycoside types are represented among its constituents and they include a pentaglycoside steroid sulfate (asterosaponin), designated henricioside A, 1 sulfatated diglycoside (laeviuscoloside A, I), 6 sulfated monoglycosides (laeviuscoloside B, C, D, E and echinasteroside A and B) with 4 variants of aglycons [cholestane; 24-methyl-26-hydroxy-; 24-hydroxymethyl- and 24-(β-hydroxyethyl)-cholestane] all having the same nuclear hydroxylation pattern, 2 non-sulfate diglycosides (laeviuscoloside F and G) with 2 monosaccharide residues attached at different positions of their aglycons (C-3 and C-24), and 2 non-sulfated monoglycosides (laeviuscoloside I and H). The stereochemistries at the side chain stereogenic centers of the steroids were based on the anal. of 1H- and 13C NMR data and comparison with those of model compds. The major steroid glycoside constituent, laeviuscoloside A showed antifungal activity and inhibited cell division of fertilized sea urchin eggs.